Luxury Catamaran Sailing ChartersTailored in every way to suit your needsLearn More

Key West and Key Largo locationsSailing the beautiful Florida Keys, Bahamas and beyondLearn More

Welcome to Calypso Sailing

Calypso Sailing was established in 1988 in the beautiful Florida Keys. With locations in both Key Largo and Key West we specialize in luxury sailing vacations on a range of Leopard Catamarans, both bareboat and Captained. Our monohull sailing charters
can take groups of 6 to 38 on day, sunset and overnight trips whilst not forgetting the iconic African Queen steamboat from the 1951 movie starring Humphrey Bogart and Katharine Hepburn which operates daily in Key Largo.

Our aim is taking care of all your cruising needs

CHARTERS

CATAMARANS

MONOHULLS

"Had a great cruise with Capt Lance and first mate Tony! Thought you would like that Tony. Highly recommend! Just as the cruise was about to end, turned into a fishing trip! Caught a 5 ft barracuda! Next trip will stay over night and do some snorkeling!"- Tony H (TripAdvisor).

"Nothing like being on a quiet sailboat, sipping wine and watching the sunset and moon-rise. I like the fact that is is a small boat, with a small group of people, so there is plenty of room to sit and move around. Pirate theme was a fun extra."- AFwifeandtraveler (TripAdvisor)

"Took a sunset sail with Capt David. He was very accommodating and was great the boat was not packed. Had a wonderful sunset and cannot feel much more relaxed than I was after this trip. Highly recommended."- Patrick O. (TripAdvisor)